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Find cheap flights from Chicago to Sicily from $291

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Sicily departing on 9/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/2
Sun 6/9

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Best Sicily Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Palermo
Palermo1 stop$626

Good to know

Low season

January

High season

September

Cheapest flight

$291
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway Airport to Palermo

FAQs - booking Sicily flights

  • Can I find direct flights from Chicago to Sicily?

    There aren’t any airlines that fly direct from Chicago to Sicily. Your best option will be to track down an airline that makes just one stop between Chicago and Sicily with a short layover. SWISS, for example, has flights from Chicago O'Hare International Airport (ORD) to Falcone Borsellino Airport (PMO) that make just one stop and get to Sicily in about 15 hours.

  • Can I get free Wi-Fi on flights from Chicago to Sicily?

    You'll be able to get free Wi-Fi on Air France that you can use to send in-flight messages to family and friends. You'll also be able to get free Wi-Fi on Delta flights after you sign up for a free SkyMiles membership.

  • Where will layovers occur when flying from Chicago to Sicily?

    Since most flights from Chicago to Sicily feature numerous stops, you may have to endure layovers at any number of locations. Some airports where layovers might take place include Frankfurt Airport (FRA), Istanbul Airport (IST), Zurich Airport (ZRH), and Lamezia Terme International Airport (SUF).

  • What can I do to make a flight from Chicago to Sicily sustainable?

    Each airline that flies from Chicago to Sicily is taking steps toward building a more sustainable business. Choose the one with the sustainability plan you like most. Turkish Airlines, for instance, has a plan that calls for the airline to become carbon-neutral in the coming years by using more fuel-friendly planes and technology to come up with shorter flight plans.

  • How does KAYAK find such low prices on flights from Chicago to Sicily?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Sicily.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Sicily?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Sicily from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Sicily?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Sicily with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Sicily?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Sicily from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Sicily

  • Morning departure is around 29% more expensive than an evening flight, on average*.
  • Anyone wishing to fly from Chicago to Sicily will be able to leave from either Chicago O'Hare International Airport (ORD) or Chicago Midway International Airport (MDW), but ORD offers more options for those searching for flights. You'll also be able to fly into either Vincenzo Bellini Catania Airport (CTA) or Falcone Borsellino Airport (PMO) in Sicily. CTA is on the southeast coast of Sicily near Catania, while PMO is situated in the northwest region near Palermo.
  • Those planning to fly from Chicago to Sicily will only need to bring a valid U.S. passport. The only time you’ll need to bring a visa is if you plan to stay in Sicily for more than 90 days.
  • Flying first class is a wonderful way to keep yourself comfortable while flying from Chicago to Sicily. Air France, Delta, and SWISS all offer great first-class accommodations to those who wish to upgrade their seats. You’ll be able to get access to everything from a lie-flat seat you can utilize for sleep to more in-flight entertainment than you would ever need, so you can stay busy on long flights to Sicily.
  • If you’re lucky enough to fly first class from Chicago to Sicily, you should be able to check bags through most airlines without paying extra fees. But if you’ll be flying to Sicily in a lower cabin class, every bag you check will be subjected to fees through airlines like Lufthansa, SWISS, and others. You may be able to keep your travel costs down by flying with just a carry-on bag.
  • Chicago O'Hare International Airport and Chicago Midway International Airport offer lounges you can use to fill time after arriving for a flight to Sicily. ORD has options like the Delta Sky Club for Delta passengers, while MDW has Club MDW available to all passengers regardless of which airline they’re flying with.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Chicago to Sicily

 
Need help choosing which airline to fly with from Chicago to Sicily? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.3
EVA AirOverall score based on 1542 reviews
8.0Food
8.2Comfort
8.6Crew
8.4Boarding
8.0Entertainment
Airline reviews

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

10.0 ExcellentDamian, Mar 2024LAX - TPE
Read more about EVA Air reviews

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant, comfortable, and entertaining. All told, ZERO issues with it. And sadly, so far the flight was WAY more comfortable than the hellhole that is "Lambug Beach Resort" at Badian Beach!

It was a pleasant fly with Eva Air from NYC to Taipei. The crew were friendly and the food was exceeded my expectation.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Overall the flight was what might be expected for a long haul flight to Asia in economy class. The cabin crew was attentive and the food was good. Boarding was fairly fast and easy. The one thing I found frustrating was the EVA app. It is terrible. Trying to do anything on it was almost impossible.

EVA would not help with ticket issue since they were purchased through a travel agency. Even though it was EVA ticket stock. Travel agency Budget Air didn't reissue ticket after airline change which I didn’t learn until trying to checkin on Christmas Day and there was no contact number for the agency to help. I will never use Budget Air to purchase flight again and disappointed in EVA’s refusal to help. Thankfully just under 12 hrs before departure someone from the agency was available to reissue tickets. I was starting to think we would not be flying and the stress trying to resolve was completely unacceptable.

seamless check in/ friendly staff, food is good, always love flying Eva Air

Very uncomfortable and crowded seats in economy. Flight attendant refused request to move to nearby unused seat with more legroom because “It was more money for that seat”. It was also near impossible to reach airline directly by phone. Waits upwards of an hour and not very helpful customer service representatives after long wait. Cannot recommend this airline.

My experience with Eva sir was good except the long walk in LA Lex, that was inconvenient for my age,

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Book cheap flights from Chicago to Sicily

Recent round-trip flight deals

9/30Mon
1 stopScandinavian Airlines
30h 35mORD-PMO
10/9Wed
1 stopScandinavian Airlines
14h 45mPMO-ORD
$626
9/30Mon
1 stopScandinavian Airlines
30h 35mORD-PMO
10/9Wed
1 stopScandinavian Airlines
14h 45mPMO-ORD
$628
9/16Mon
1 stopTurkish Airlines
29h 05mORD-CTA
9/23Mon
1 stopTurkish Airlines
21h 25mCTA-ORD
$721
10/1Tue
1 stopTurkish Airlines
28h 45mORD-PMO
10/24Thu
1 stopTurkish Airlines
31h 25mPMO-ORD
$725
8/16Fri
2 stopsDelta
21h 45mORD-PMO
8/29Thu
2 stopsDelta
17h 55mPMO-ORD
$918
8/12Mon
1 stopLufthansa
18h 25mORD-PMO
11/10Sun
2 stopsLufthansa
32h 44mPMO-ORD
$936
7/13Sat
2 stopsAir France
36h 40mORD-PMO
8/24Sat
1 stopAir France
35h 25mPMO-ORD
$967
10/30Wed
2 stopsAir France
43h 55mMDW-CTA
11/3Sun
2 stopsAir France
29h 33mCTA-MDW
$980
7/30Tue
2 stopsDelta
20h 10mORD-PMO
8/13Tue
2 stopsDelta
24h 19mPMO-ORD
$994
9/6Fri
1 stopLufthansa
19h 30mORD-CTA
9/14Sat
1 stopLufthansa
13h 30mCTA-ORD
$1,156

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Recent one-way flight deals

9/4Wed
3 stops
44h 02mMDW-PMO
$291
9/4Wed
3 stops
44h 02mMDW-PMO
$294
9/9Mon
3 stops
28h 12mMDW-PMO
$327
9/4Wed
1 stopTurkish Airlines
28h 45mORD-PMO
$718
9/10Tue
1 stopTurkish Airlines
28h 45mORD-PMO
$726
9/17Tue
2 stopsDelta
25h 04mMDW-PMO
$1,001
8/1Thu
2 stopsDelta
17h 16mMDW-PMO
$1,051
9/11Wed
1 stopLufthansa
12h 30mORD-PMO
$1,075
9/12Thu
1 stopLufthansa
12h 30mORD-PMO
$1,120
9/6Fri
2 stopsAir France
14h 26mMDW-PMO
$1,470

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Last minute flights from Chicago to Sicily

Last minute flight, train and bus deals

5/4Sat
multi-stopITA Airways
32h 40mORD-CTA
5/12Sun
multi-stopITA Airways
24h 55mCTA-ORD
$987
5/7Tue
multi-stop
12h 20mORD-PMO
5/28Tue
multi-stop
50h 35mPMO-ORD
$1,175
5/7Tue
multi-stop
16h 15mORD-PMO
5/28Tue
multi-stop
36h 45mPMO-ORD
$1,199
5/6Mon
multi-stop
15h 25mORD-PMO
5/27Mon
multi-stop
31h 40mPMO-ORD
$1,344
5/6Mon
multi-stop
17h 10mORD-PMO
5/27Mon
multi-stop
29h 35mPMO-ORD
$1,396
5/6Mon
multi-stopTAP AIR PORTUGAL
21h 50mORD-PMO
5/27Mon
multi-stopTAP AIR PORTUGAL
55h 55mPMO-ORD
$1,403
5/7Tue
multi-stopLufthansa
12h 35mORD-PMO
5/28Tue
multi-stopLufthansa
31h 40mPMO-ORD
$2,059
5/4Sat
multi-stopAir France
17h 00mMDW-CTA
5/12Sun
multi-stopAir France
23h 01mCTA-MDW
$2,157
5/4Sat
multi-stopAir France
17h 00mMDW-CTA
5/12Sun
multi-stopAir France
23h 01mCTA-MDW
$2,158
5/6Mon
multi-stopDelta
21h 30mMDW-PMO
5/27Mon
multi-stopDelta
17h 56mPMO-MDW
$2,168

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